Not many bands could pull off a number about a man and his four-track tape recorder, but such is the creative genius of Mr. Michael Gordon. Mike wrote the song after someone stole his four-track machine during Springfest at Goddard College one year. The lyrics recount his lament over the theft. Mike once mentioned in an interview that a third verse exists that references driving around in a pickup truck and stealing the four-track back.

For many years, it was thought that the song debuted in 1991, although it was known to have been mentioned on stage as early as 1988. Listen to the first set of April 22 from that year; Trey mentions several new songs, including “The Four-Track Song.” This would eventually become “Poor Heart.” However, with the release of Colorado '88, it was discovered that "Poor Heart" was actually played as early as 8/4/88. It is believed that “Poor Heart” was played on at least one other occasion in 1988 (8/27/88), before being put in the pen until 4/22/91. Neither of these '80s versions of “Poor Heart” circulate, though it is said that they are substantially similar to the “modern” versions, only a touch slower. While it is true that almost all “modern” versions of “Poor Heart” are performed in the same up-tempo, bluegrass fashion – and, since 8/15/98, exclusively in the first set – the few versions that have strayed from this pattern are highly memorable.

The band’s greatest on-stage experimentations with “Poor Heart” took place in the fall of 1995. On 11/19, the band broke into a slower bluegrass number near the beginning of the first set. Fans were surprised when the “Poor Heart” lyrics were sung over this groove. The song was again performed this way in Landover on 11/22. Three nights later, the band played the original “Poor Heart” to kick off the first set in Hampton. Then, to confound matters, the second set ended with the slow version! Never willing to let a good joke pass, the band then began the encore with an even slower “Poor Heart” before stopping and asking the audience: “Get it?” Many did, as they realized that the band had the power to change even the most static of songs. While the slow “Poor Heart” has not been performed since, fans have reported hearing it soundchecked (for example, 12/8/95 and 8/4/96).

The most radical and different Phish interpretation of "Poor Heart” has never been played during a show. Those fortunate enough to have a copy of the 5/5/93 soundcheck can relish the “Poor Heart Blues,” a rocking adaptation based on the musical progression used in “Funky Bitch” that has been known to make listeners laugh and dance at the same time.

You won't steal my poor heart again
You won't steal my poor heart again
You won't steal my tape recorder
I'll call the Lord and he'll put you in the pen
You won't steal that thing again

I didn't even know your name or what was your game
But stealin' things has sure brought you to fame
I wanna know if you stole mine
It was one of a kind and I'm sayin' if you're to blame
Your life will never be the same

You won't steal my poor heart again
You won't steal my poor heart again
You won't steal my tape recorder
I'll call the Lord and he'll put you in the pen
You won't steal that thing again

I can't track you anymore
Detective work has sure become a bore
So tell me what you did with it
And stop this shit, give up yourself
Before they come knockin' at your door

You won't steal my poor heart again
You won't steal my poor heart again
When I feel the blade of that Cupid sword
I'll call the Lord and he'll put you in the pen
You won't steal that thing again
You won't steal my poor heart again